Dyestuffs of the anthraquinone series



Patented Mar. 14, 1939 UNITED STATES PATENT OFFICE Werner Zerweck, Ernst Heinrich,

and Otto Trosken, Frankfort-on-the-Main-Fechenheim, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application March 4, 1938, Serial No. 193,916. In Germany March 5, 1937 3 Claims.

Our present invention relates to dyestufis of the anthraquinone series, more particularly to those of the general formula:

(d NHQ A lGH-R wherein R stands for a member selected from the group consisting of alkyl, cycloalkyl and aryl, aryl meaning a radicle of the benzene series.

5 The new dyestuffs may be prepared for instance by condensing 1-amino-4-halogenanthraquinone- 2-sulfonic acid chloride with imino-diacetic acid (or with amino-acetic acid or NH3, followed by after treatment with chloroacetic acid) and replacing the halogen atom in the l-position of the condensation product formed by the radicle of a suitable amine.

It is surprising that the new dyestuffs possess the properties of acid wool dyestuffs and that they have a solubility in water sufficient for such dyestuffs, in spite of the absence of sulfo groups in the molecule. They are distinguished by a surprisingly good levelling power which is better than that of the corresponding known dyestuffs. containing a sulfo group instead of the group:

In order to further illustrate our invention the following examples are given, the parts being by weight and all temperatures in degrees centigracle, but we wish it, however, to be understood that our invention is not limited to the examples given nor to the exact conditions stated therein.

Emample 1 temperature for some hours, until a test gives a. clear solution in water. The dioxane and the alcohol are removed by distillation with steam, the aqueous solution is filtered and the sulfoneamide formed of the formula:

orirooon l is precipitated by the addition of sodium chloride and purified by recrystallization from water.

10 parts of this sulfoneamide compound are dissolved in about 1000 parts of water, then 12 parts of aniline, 5 parts of sodium bicarbonate and 1 part of copper sulfate are added and the mixture is heated to about -90 for some hours. When the formation of the dyestuff is complete, the solution is filtered and the dyestufi formed of the formula:

1 GHQ-CO 0H SOg-N CHz-OOOH 0 NHa OHPCOOH SOz-N OHr-COOH im-O-meooom which dyes wool clear greenish blue shades 0 good levelling power and good fastness properties.

The analogous dyestuif which contains the acetylamino group in the 3-position of the benzene nucleus yields on Wool reddish blue shades of similar good properties.

Example 2 GET-CO OH S O2N CHFCOOH is precipitated by the addition of sodium chloride, filtered off and dried. It dissolves in concentrated sulfuric: acid With a yellowish-brown color which is turned to blue by the addition of paraformaldehyde. The dyestuif dyes Wool reddish blue shades of good fastness properties.

By replacing hexahydroaniline by the corresponding amount of isopropylamine or sec.-butylamine similar dyestuffs are obtained which yield on wool likewise reddish blue shades of good levelling power and good fastness properties.

We claim:

1. The dyestuffs of the anthraquinone series of the formula:

0 NH, OHPCOOH o NH-R wherein R stands for a member selected from the group consisting of alkyl, cycloalkyl and aryl, aryl meaning a radicle of the benzene series, which dyestuffs yield on Wool blue to green shades of good levelling power and good fastness properties.

2. The dyestuff of the anthraquinone series of the formula:

S OzN CHPC O OH which dyestufi dyes Wool and acetate artificial silk clear blue shades of very good levelling power and good fastness properties.

3. The dyestuff of the anthraquinone series of the formula:

H2COOH d IH-O-NH-C 0 CH3 which dyestuff dyes Wool clear greenish blue shades of good levelling power and good fastness properties.

| OHr-C OOH WERNER ZERWECK. ERNST HEINRICH. OTTO TROSKEN. 

